[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[O:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2B(O)O)[CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:19]=2[O:10][CH2:11][CH2:12][CH2:13]3)[C:5]([F:9])=[CH:4][N:3]=1A batch with 2,4-dichloro-5-fluoropyrimidine (565 mg; 3.28 mmol; Aldrich Chemical Company Inc.), 3,4-dihydro-2H-chromen-8-ylboronic acid (643 mg; 3.61 mmol; Parkway Scientific LLC) and bis(triphenylphosphine)palladium(II)chloride (230 mg; 0.33 mmol; Aldrich Chemical Company Inc.) in 1,2-dimethoxyethane (5.4 ml) and 2M solution of potassium carbonate (4.9 ml) was degassed using argon. The batch was stirred under argon for 16 hours at 90° C. After cooling the batch was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic phase was dried (sodium sulfate), filtered and concentrated. The residue was purified by chromatography (hexane/ethyl acetate 2%-20%) to give the desired product (701 mg; 2.57 mmol).
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